The paper contributes by proposing an analytical approach that allows for the identification of patterns of participation in education and training and the labour market, through empirical measurement of the number of transitions and distinct trajectories traversed by groups of individuals. To illustrate the value of the approach, we focus on an original survey data set of a 2009/2010 cohort of participants in the apprenticeship system in South Africa. The paper demonstrates that despite a clear shift in access, transition into the apprenticeship system remains strongly determined by race and gender. Race, class and gender likewise determine those who experience more complex transitions to the labour market. The methodological and analytical approach thus allows a clear identification of the location and the nature of potential structural inequalities in a pathway system. This ability is critical in many country contexts where social inequalities continue to hamper growth and development, but the ways in which these manifest structurally in skilling systems are often poorly identified and understood, and consequently, blockages are poorly addressed.